Synthesis of Piperidines from Z-α,β-Unsaturated Diazoketones

Synthesis of Piperidines from Z-α,β-Unsaturated Diazoketones

Rosset, Isac G.; Burtoloso, Antonio C. B.

Abstract:

Piperidine systems are highly widespread in many natural products of great pharmaceutical interest. These systems have many interesting biological activities, such as anticancer and anti-HIV. In this work, we describe the stereoselective preparation of Z-α,β-unsaturated diazoketones from aldehydes and their conversion to substituted dihydropyridin-3-ones like 3 in just one step after an intramolecular N-H insertion reaction. The application of this chemistry in the direct synthesis of the natural 3,4,5- trihydroxypiperidine 4 is also described (Fig 1).

Piperidine systems are highly widespread in many natural products of great pharmaceutical interest. These systems have many interesting biological activities, such as anticancer and anti-HIV. In this work, we describe the stereoselective preparation of Z-α,β-unsaturated diazoketones from aldehydes and their conversion to substituted dihydropyridin-3-ones like 3 in just one step after an intramolecular N-H insertion reaction. The application of this chemistry in the direct synthesis of the natural 3,4,5- trihydroxypiperidine 4 is also described (Fig 1).

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013915103424

Referências bibliográficas

• [1] 1Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721–4722.
• [2] 2Pak, C. S.; Lee, G. H. J. Org. Chem. 1991, 56, 1128–1133.
• [3] 3Sekioka, T.; Shibano, M.; Kusano, G. Nat. Med. 1995, 49, 332–335.
• [4] 4Rosset, I. G. Burtoloso A. C. B. J. Org. Chem. 2013, ASAP, DOI:
• [5] 10.1021/jo401191s

Como citar:

Rosset, Isac G.; Burtoloso, Antonio C. B.; "Synthesis of Piperidines from Z-α,β-Unsaturated Diazoketones", p-252-252. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013915103424